Manufacture of vat dyestuffs of the anthraquinone-acridone series



10 converted intoacridone derivatives Patented Nov. 6, 1928.

UNITED STATES PATENT I OFFICE.

OSKAR UNGEB, OF LUDWIGSHAFENFON-THE-IRHINE, AND GEORG BOHNER, F FRIED- BICHSFELD, GERMANY, ASSIGNORS TO GRASSELLI"DYESTUFF CORPORATION, OF NEW YORK, N. Y., A CORPORATION OF DELAWARE.

MANUFACTURE OF VAT DYESTUFFS THE ANTHRAQUINOIi'E-ACRIDONE SERIES.

Ho Drawing. Application filed October 25, 1926, SerialNo. 144,169, and in Germany October 29, 1925. i

It has been disclosed in the German Patent No. 237,236 that vat dyestuiis of the anthraquinone series can be prepared from 1-nitroor 1-chlor-anthraquinone-2-carboxylic acid. 5 According to the said process the acids are first converted into l arylamino-anthraquinone-2-carboxylic acids; in a second stage these acids, either directly or after being converted for example into acid halogenids, are

b ment with condensing agents. The (iierman Patents Nos. 237,237 and 248,170 describe IllOdlfiCfltlOIlS-Of this two-stage process for the production of vatdycstufi's (see also U.

S. Patents 1,002,066 and 1,011,068).

We have now found that the condensation j of l-cholor-antraquinone-2-carboxylic acids with arylamines and the conversion of the resulting 1-arylamino-anthraquinone-2-carboxylic acids into the a'cridones can be carried out in-a single -stage,s0 that the valuable acridones can-be prepared in a much more advantageous" manner. than was hitherto possible. f

According to our invention the initial materials, i e. the 1-cholor anthraquinone-2-- carboxylic acid and the aryl-amine, are heated in an inert organic solvent until the formation of thedyestufi has taken place. his not necessary to carry out the operation in the resence of condensing agents or catalytic y acting materials, but it is often advantageous to employ such substances, as in their presence the reaction proceeds more rapidly and with better yields.

Most advantageously mild condensing agents es cially such 0 an acid nature, are employe As examples we mention borax, potassium bisulfate, oxalic acid, boric acid, iajisenious acid, antimonious acid and the The following examples will further illustrate how the present invention may be carried out in practice, but the invention is not limited to these examples. The parts are by weight.

EmampZe 1. 300 parts of nitro 28.6 parts of 1- chlor-anthraquinone-2-carboxylic acid and 17.2 parts of beta-naphtlzilylamine are boiled under a reflux cooler un the'formation of the dyestufi is finished. The mass is then allowed to cool, whereupon the separated treatcrystals are filtered oif byfsuction and freed from solvent in the usual manner. The product so obtained is identical with that described in the U. S. Patent No. 1,011,068, and corresponds to the formula Emampilefl.

300 parts of napthalene, 28.6 parts of 1-chlor-anthraquinone-2-earboxylic acid, 15

parts of oxalic acid and 17.2 parts of betanaphthylamine are treated as described in Example 1. The product is allowed to cool and freed from naphthalene by treatment with an organic solvent, whereby the same dyestufi as described in the foregoing example is obtained in glossy, red leaflets.

I Example 3.

boxylic acid is no longer present. The product is worked up as described in Example 1. The product, corresponding to the formula:

and the yield are the same as described in Example 3 of theGerman Patent No. 237 ,236.

Example .4.

300 parts of trichlorbenzene, 28.6 parts of 1-chlor-anthraquinone-2-carboxylic acid, 8.2 parts of anhydrous sodium acetate and 17.2

ion

parts of beta-naphthylamine are boiled until acetatic acid is no longer evolved, whereupon 124 parts of boric acid are addedtical to those obtained according to Exam-.

ple 1.

Example 5.

300 parts of trichlorbenzene, 28.6 parts of l-chlor-anthraquinone-2-carboxylic acid, 24: arts of borax and 17.2 parts of beta nap thylamine are boiled under a reflux cooler until unaltered l-chlor-anthraquinone- Q-carboxylic acid is no longer present. The product is worked up in the manner described ahove and is identical with that described in Example 1.

Instead of the condensing agents mentioned in the foregoing. examples for example potassium bisulfate, phthalic acid, henzoic acid, arsenious acid and the like may be employed.

'in heating Weclaim: r 1 a 1. The process of preparing vat dyestuffs of the anthraquinone series which consists 1n heatin a 1-chlor-anthraquinone-2-carboxylie acid and an arylamine in an inert organic solvent until the formation of dyestuil has taken place.-

2. The process of preparing vat dyestufis of the anthraquinone series which consists a 1-chlor anthraquinone-2-carboxylic acid and an arylamine in aninert organic solvent in the presence of a weakly acid'condensing agent until the formation of dyestufl' has taken place.

3. The process of preparing a vat dyestuff of the anthraquinone series which consists in heating l-chlor-anthraquinone-2-carboxylic acid with beta-naphtliylamine in an 7 inert organic solvent the formation of dyestuif has taken lace.

In testimony w ereof we have hereunto set our hands. 7

osm s rens. enoae semen. 

